Classifications

• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
  • C11B9/00—Essential oils; Perfumes
  • C11B9/0007—Aliphatic compounds
  • C11B9/0011—Aliphatic compounds containing S
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
  • C11B9/00—Essential oils; Perfumes
  • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
  • C11D1/02—Anionic compounds
  • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
  • C11D1/123—Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/50—Perfumes
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
  • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
  • D06M13/005—Compositions containing perfumes; Compositions containing deodorants
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
  • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
  • D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
  • D06M13/248—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing sulfur
  • D06M13/256—Sulfonated compounds esters thereof, e.g. sultones

Definitions

• Fragrances are used for various products of daily use for the purpose of producing a feeling of luxuriousness, a feeling of security, a feeling of expecting effectiveness or the like.
• a characteristic scent gives a product identification effect and customer attracting power.
• imparting a scent to products is performed by using a fragrance composition obtained by mixing multiple fragrance materials to control a balance or retainability of scents or the like.
• the present invention provides a fragrance composition and a method for imparting a scent excellent in scent retaining performance on an object.
• the present invention relates to a fragrance composition containing, (A) a fragrance compound [hereinafter referred to as component (A)], and (B) a compound represented by the following formula 1 [hereinafter referred to as component (B)],
• Component (A) has a Log P of preferably 1 or more, more preferably 2 or more and further preferably 3 or more, and preferably 7 or less, more preferably 5 or less and further preferably 4 or less from the viewpoints of dispersion stability and scent retaining performance.
• ketones examples include methylheptenone, dimethyloctenone, 3-octanone, hexylcyclopentanone, o-tert-butylcyclohexanone, dihydrojasmone, 2,2,5-trimethyl-5-pentylcyclopentanone (VELOUTONE, trade name by Firmenich S.A.), 2-(2-(4-methyl-3-cyclohexen-1-yl) propyl)cyclopentanone (Nectaryl, trade name by Givaudan S.A.), ionones, methyl ionone, ⁇ -methyl ionone, damascones, ⁇ -damascone, ⁇ -damascone, 1-(2,4,4-trimethyl-2-cyclohexyl)-trans-2-butanone (Isodamascon, trade name by Symrise AG), damascenones, 1-(5,5-dimethyl-1-cyclohexen-1-yl
• esters used as a fragrance material include an aliphatic carboxylic acid ester, an aromatic carboxylic acid ester and other carboxylic acid esters.
• Examples of the natural essential oil and the natural extract include orange, lemon, lime, bergamot, petitgrain, neroli, vanilla, mandarin, peppermint, spearmint, lavender, lavandin, chamomile, rosemary, eucalyptus, sage, basil, rose, rockrose, geranium, jasmine, ylang-ylang, anise, clove, ginger, nutmeg, cardamom, cedar-wood, cypress, vetiver, guaiac wood, patchouli, lemongrass, labdanum, galbanum, olibanum, gurjun balsam or the like.
• component (A) in the vesicle also contributes to suppressed volatilization of component (A).
• component (B) is considered to be excellent in the effect of delivering component (A) to an object in water. It is considered that these suppress volatilization of component (A), thus improving scent retaining performance.
• the acting mechanism of the present invention is not limited thereto.
• R 1 and R 2 each represent preferably a branched-chain hydrocarbon group having a main chain and a side chain, the side chain having 2 or more and further 3 or more, and 10 or less, 8 or less, further 6 or less and further 4 or less carbons.
• R 1 and R 2 each represent more preferably a branched-chain hydrocarbon group having a main chain and a side chain, the side chain having 3 or 4 carbons.
• hydrocarbon groups of R 1 and R 2 are branched-chain hydrocarbon groups, they may each be a group derived from a Guerbet alcohol from the viewpoints of scent retaining performance and availability.
• R 1 and R 2 may have the same or different numbers of branch carbons and each have 1 or more, and preferably 3 or less and furthermore preferably 2 or less branch carbons from the viewpoint of scent retaining performance.
• R 1 and R 2 each preferably have one branch carbon from the viewpoint of scent retaining performance.
• a number of branch carbons is a total of numbers of tertiary carbon atoms and quaternary carbon atoms in a branched-chain alkyl group.
• R 1 and R 2 each represent preferably a branched-chain alkyl group selected from a branched-chain decyl group and a branched-chain dodecyl group and more preferably a branched-chain decyl group from the viewpoint of scent retaining performance.
• the branched-chain decyl group include 2-propylheptyl group, a group derived from a decyl alcohol manufactured by KH Neochem Co., Ltd. or the like, and 2-propylheptyl group is preferable.
• Examples of the branched-chain dodecyl group include 2-butyloctyl group or the like.
• the hydrocarbon groups of R 1 and R 2 in the formula 1 may be the same or different.
• the case where the hydrocarbon groups of R 1 and R 2 are different is preferable from the viewpoint of dispersibility in water. Further, the case where the hydrocarbon groups of R 1 and R 2 are the same is preferable from the viewpoint of scent retaining performance.
• R 1 and R 2 in the formula 1 may have the same or different numbers of carbons. The case where R 1 and R 2 have different numbers of carbons is preferable from the viewpoint of dispersibility in water. Further, the case where R 1 and R 2 have the same number of carbons is preferable from the viewpoint of scent retaining performance.
• the fragrance composition of the present invention can contain a compound represented by the formula 1 in which R 1 and R 2 represent a hydrocarbon group of the same structure and a compound represented by the formula 1 in which R 1 and R 2 represent hydrocarbon groups of different structures as component (B).
• M is preferably an alkali metal ion or an alkanolammonium ion, more preferably a sodium ion, a potassium ion, a triethanolammonium ion, a diethanolammonium ion or a monoethanolammonium ion and further preferably a sodium ion from the viewpoint of dispersibility in water.
• Component (B) of the present invention is preferably a compound represented by the formula 1-1 below.
• the present invention provides a fragrance composition containing a compound represented by the formula 1-1 below as component (B).
• a compound of the formula 1-1 is a compound of the formula 1 in which x1 and x2 each represent 0.
• Component (B) can be synthesized by a publicly-known method. For example, it can be obtained by reacting a maleic acid diester obtained by reacting maleic anhydride and an alcohol with hydrogen sulfite. At that time, alcohols of different carbon numbers or structures can be used to obtain a compound of the formula 1 in which R 1 and R 2 represent hydrocarbon groups of different structures. Component (B) can be synthesized, for example, by the processes described in Examples 2 to 3 of US-A 2007/0214999.
• Component (B) is preferably a di(2-propylheptyl) sulfosuccinate from the viewpoints of dispersibility in water and scent retaining performance.
• the salt is preferably an alkali metal salt or an alkanolamine salt, more preferably a sodium salt, a potassium salt, a triethanolamine salt, a diethanolamine salt or a monoethanolamine salt and further preferably a sodium salt.
• a proportion of component (A) relative to 100 parts by mass of component (B) in the fragrance composition of the present invention is preferably 10 parts by mass or more, more preferably 12.5 parts by mass or more and further preferably 15 parts by mass or more, and preferably 100 parts by mass or less, more preferably 60 parts by mass or less, further preferably 50 parts by mass or less and furthermore preferably 30 parts by mass or less from the viewpoints of dispersibility in water and scent retaining performance.
• the fragrance composition of the present invention can also optionally contain a surfactant other than component (B).
• a proportion of component (B) in all surfactants in the fragrance composition of the present invention is preferably 80 mass % or more, more preferably 90 mass % or more and further preferably 99 mass % or more, and preferably 80 mass % or less, more preferably 90 mass % or less and further preferably 100 mass % or less from the viewpoints of dispersibility in water and scent retaining performance.
• the fragrance composition of the present invention preferably contains water.
• the fragrance composition of the present invention can contain water in an amount of, for example, 85 mass % or more, further 90 mass % or more and further 95 mass % or more, and 98 mass % or less, further 97 mass % or less and further 96 mass % or less.
• the fragrance composition of the present invention may be a fragrance composition obtained by mixing components (A) and (B) with water, for example, a dispersion liquid or a solubilization liquid obtained by dispersing or solubilizing component (A) in water in the presence of component (B).
• the fragrance composition used in the method for imparting a scent of the present invention may be a fragrance composition obtained by mixing components (A) and (B) with water, for example, a dispersion liquid or a solubilization liquid obtained by dispersing or solubilizing component (A) in water in the presence of component (B).
• the fragrance composition is used such that a proportion of component (A) relative to 100 parts by mass of component (B) is preferably 10 parts by mass or more, more preferably 12.5 parts by mass or more and further preferably 15 parts by mass or more, and preferably 100 parts by mass or less, more preferably 60 parts by mass or less, further preferably 50 parts by mass or less and furthermore preferably 30 parts by mass or less from the viewpoints of dispersibility in water and scent retaining performance.
• % o.w.f. stands for % on the weight of fabric and means a percentage of a mass of component (B) relative to a mass of the fibers.
• the treatment liquid of the present invention can be used such that an amount of component (B) relative to the fibers falls within the above range.
• the method for imparting a scent of the present invention can be carried out by being incorporated into laundering processes of the fibers, for example, cloth or a textile.
• the laundering processes may be washing, rinsing and dewatering treatments of the fibers.
• the fragrance composition of the present invention can be applied to the fibers such that component (B) is in a predetermined amount.
• the towels were dewatered for 2 minutes in a dewatering tub of a twin tub washing machine (model number VH-52G(H) manufactured by TOSHIBA CORPORATION) and dried in a room at 23° C./45% RH.
• the treatment liquid prepared here is also a fragrance composition.
• a fragrance composition of an example has a higher value of a degree of scent retention A (24/4) than a comparative example as shown in Evaluation 2, and is thus found to have a higher effect of maintaining scent retaining performance over time.
• a fragrance composition of an example attains more excellent results than a comparative example in both evaluations 1 and 2, and an example is thus found to exhibit higher scent retaining performance also in the treatment method for Table 2 different from that for Table 1.
• a 5 mass % aqueous dispersion liquid of a fragrance composition shown in Table 3 was diluted with an aqueous calcium chloride solution (equivalent to 4° DH) such that the concentration of component (B) was the concentration shown in Table 3 to obtain a liquid for evaluations.
• 80 ml of the liquid for evaluations was placed in a standardized bottle No. 11 (5-130-07 by AS ONE Corporation), and a paper towel (super absorbent kitchen towel Elleair of 12 cm ⁇ 12 cm) was rolled up and placed standing in the bottle containing this liquid for evaluations. At that time, the kitchen towel was placed such that a lower portion thereof was immersed in the liquid and an upper portion thereof was exposed from a liquid surface. After that, it was left alone in a room at 23° C./35% RH.
• a fragrance composition of an example attains more excellent results than a comparative example in both evaluations 1 and 2, and an example is thus found to exhibit higher scent retaining performance also in a usage form considering spatial volatilization of a fragrance composition such as a standing-type air refreshing agent.
• component (B) a di(2-butyloctyl) sulfosuccinate, a dodecyl/2-butyloctyl-sulfosuccinate, an octyl/cetyl-sulfosuccinate or a dodecyl/3-nonenyl-sulfocuccinate is used as component (B) in a fragrance composition in Tables 1 to 3 instead of component (B) in the tables, the effect of the present invention can be obtained in the same manner.
• Scent retaining performance evaluation 1 (scent retaining performance by paired evaluation) was performed in the same manner as in example 1 and comparative example 1, provided that fragrance compositions and treatment conditions were as in Table 4. The evaluation results are shown in Table 4.
• Scent retaining performance evaluation 2 (scent retaining performance by point-addition evaluation) was performed in the same manner as in example 1 and comparative example 1, provided that fragrance compositions and treatment conditions were as in Table 5 and dewatering in the method for treating towel in (2) was carried out by using a dewatering tub of a twin tub washing machine (model number PS-55AS2 manufactured by Hitachi, Ltd.). The evaluation results are shown in Table 5.
• Scent retaining performance evaluation 1 (scent retaining performance by paired evaluation) was performed in the same manner as in example 2 and comparative example 2, provided that fragrance compositions and treatment conditions were as in Table 6. The evaluation results are shown in Table 6.
• Scent retaining performance evaluation 1 (scent retaining performance by paired evaluation) was performed in the same manner as in example 3 and comparative example 3, provided that fragrance compositions and treatment conditions were as in Table 8. The evaluation results are shown in Table 8.

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• Chemical & Material Sciences (AREA)
• Engineering & Computer Science (AREA)
• Life Sciences & Earth Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Wood Science & Technology (AREA)
• Organic Chemistry (AREA)
• Textile Engineering (AREA)
• Fats And Perfumes (AREA)

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• 2022
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  • 2022-06-22 US US18/572,401 patent/US12275915B2/en active Active
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